Clopidogrel Bisulfate
(S)-Clopidogrel · methyl (2s)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate · Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (αS)- · CLOPIDOGREL · Chlopidogrel · ClopidogrelHcl · Clopidogrel–d4 · Clopidogrel API
Identifikatoren & physikalische Daten
| CAS No. | 113665-84-2 |
|---|---|
| Summenformel | C16H18ClNO6S2 |
| Durchschnittliche Molmasse | 419,9 g/mol |
| Monoisotopische Masse | 419,0264073 g/mol |
| SMILES | COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1.O=S(=O)(O)O |
| InChIKey | FDEODCTUSIWGLK-RSAXXLAASA-N |
| PubChem CID | 115366 |
| ChEMBL | CHEMBL1083385 |
| EC No. | 601-679-1 |
| DTXSID | DTXSID601016080 |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 141 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 463 |
| Human Drugs | LactationBreast FeedingMilk, HumanPlatelet Aggregation InhibitorsPurinergic P2Y Receptor AntagonistsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Collision Cross Section | 167.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 423.7±45.0 °C(Predicted) |
| Dichte | 1.317±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO: 50mg/ml in DMSO |
| Aggregatzustand | Oil |
| pKa (Säurekonstante) | 4.56±0.20(Predicted) |
| Farbe | Colorless to light yellow |
| Henry-Konstante | 4.5×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | InChI=1/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/s3 |
| InChIKey | GKTWGGQPFAXNFI-UJHUVDBMNA-N |
| SMILES | [C@@H](C1C=CC=CC=1Cl)(N1CCC2SC=CC=2C1)C(=O)OC |&1:0,r| |
| CAS Datenbank | 113665-84-2(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH290 (17.4%): May be corrosive to metals [Warning Corrosive to Metals]P203, P234, P260, P261, P263, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P363, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 86 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | REACH registered substance: (S)-( )-Methyl (2-chlorophenyl)(6,7-dihydro-4H-thieno(3,2-c)pyrid-5-yl)acetate bisulfate (EC: 601-679-1) |
| Hazard Classes and Categories | Acute Tox. 4 (25.6%)Acute Tox. 4 (100%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Clopidogrel bisulfatevLess-DILI-concern7Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| R-Sätze (R) | 22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrstoffdaten | 113665-84-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Clopidogrel was launched in the US as a potent inhibitor of platelet aggregation for the preventive management of secondary ischemic events, including MI, stroke and vascular deaths. Clopidogrel can be synthesized in 4 steps (including an optical resolution to the S active enantiomer) from 2-(2- ch1orophenyl)-glycine, the key step being the cyclization to thienopyridine with formaldehyde and acetic acid. Clopidogrel belongs to the original chemical class of Ticlopidine, but shows fewer side effects (in particular, bone-marrowsuppressing effects) at the dosage generally used. Like Ticlopidine, it is an Adenosine diphosphate (ADP) antagonist acting at the purinergic P2y receptor. In in vivo experiments with rabbits, Clopidogrel shows a maximal antiaggregant effect at 20mg/kg po, reducing adhesion of platelets to the vascular subendothelium ; moreover, it reduces myointimal thickening occuring after endothelial injury of rat carotid artery. Clopigrel does not affect platelet aggregation in vitro ; actually, its in vivo activity is highly dependent on hepatic metabolism. The results of a CAPRIE trial (Clopidogrel versus Aspirin in patients at risk of ischemic events) demonstrated that Clopidogrel was well tolerated and more effective than aspirin.
History
Clopidogrel, sold under the brand name Plavix among others, is an antiplatelet medication used to reduce the risk of heart disease and stroke in those at high risk. Clopidogrel was discovered by Dr Fernand Eloy, it was patented in 1982, and approved for medical use in 1997. It is on the World Health Organization's List of Essential Medicines.
Verwenden
anthelmintic, antiparasitic, antimite